An 8 by 8 checkerboard has alternating black and white squares. How many distinct squares, with sides on the grid lines of the checkerboard (horizontal and vertical) and containing at least 5 black squares, can be drawn on the checkerboard?

[asy]
draw((0,0)--(8,0)--(8,8)--(0,8)--cycle);
draw((1,8)--(1,0));
draw((7,8)--(7,0));
draw((6,8)--(6,0));
draw((5,8)--(5,0));
draw((4,8)--(4,0));
draw((3,8)--(3,0));
draw((2,8)--(2,0));
draw((0,1)--(8,1));
draw((0,2)--(8,2));
draw((0,3)--(8,3));
draw((0,4)--(8,4));
draw((0,5)--(8,5));
draw((0,6)--(8,6));
draw((0,7)--(8,7));
fill((0,0)--(1,0)--(1,1)--(0,1)--cycle,black);
fill((2,0)--(3,0)--(3,1)--(2,1)--cycle,black);
fill((4,0)--(5,0)--(5,1)--(4,1)--cycle,black);
fill((6,0)--(7,0)--(7,1)--(6,1)--cycle,black);
fill((0,2)--(1,2)--(1,3)--(0,3)--cycle,black);
fill((2,2)--(3,2)--(3,3)--(2,3)--cycle,black);
fill((4,2)--(5,2)--(5,3)--(4,3)--cycle,black);
fill((6,2)--(7,2)--(7,3)--(6,3)--cycle,black);
fill((0,4)--(1,4)--(1,5)--(0,5)--cycle,black);
fill((2,4)--(3,4)--(3,5)--(2,5)--cycle,black);
fill((4,4)--(5,4)--(5,5)--(4,5)--cycle,black);
fill((6,4)--(7,4)--(7,5)--(6,5)--cycle,black);
fill((0,6)--(1,6)--(1,7)--(0,7)--cycle,black);
fill((2,6)--(3,6)--(3,7)--(2,7)--cycle,black);
fill((4,6)--(5,6)--(5,7)--(4,7)--cycle,black);
fill((6,6)--(7,6)--(7,7)--(6,7)--cycle,black);
fill((1,1)--(2,1)--(2,2)--(1,2)--cycle,black);
fill((3,1)--(4,1)--(4,2)--(3,2)--cycle,black);
fill((5,1)--(6,1)--(6,2)--(5,2)--cycle,black);
fill((7,1)--(8,1)--(8,2)--(7,2)--cycle,black);
fill((1,3)--(2,3)--(2,4)--(1,4)--cycle,black);
fill((3,3)--(4,3)--(4,4)--(3,4)--cycle,black);
fill((5,3)--(6,3)--(6,4)--(5,4)--cycle,black);
fill((7,3)--(8,3)--(8,4)--(7,4)--cycle,black);
fill((1,5)--(2,5)--(2,6)--(1,6)--cycle,black);
fill((3,5)--(4,5)--(4,6)--(3,6)--cycle,black);
fill((5,5)--(6,5)--(6,6)--(5,6)--cycle,black);
fill((7,5)--(8,5)--(8,6)--(7,6)--cycle,black);
fill((1,7)--(2,7)--(2,8)--(1,8)--cycle,black);
fill((3,7)--(4,7)--(4,8)--(3,8)--cycle,black);
fill((5,7)--(6,7)--(6,8)--(5,8)--cycle,black);
fill((7,7)--(8,7)--(8,8)--(7,8)--cycle,black);

[/asy]
Solution: No $1\times1$ squares or $2\times2$ squares contain five black squares. Every square which is $4\times4$ or larger does. However, a $3\times3$ square will only contain 5 black squares if its upper left corner is black. We can choose the upper left corner of a $3\times3$ square in $6\cdot6=36$ ways, but for only half of these squares will the upper left corner be black. Therefore, there are $36/2=18$ $3\times3$ squares containing at least 5 black squares. We can choose the position of the upper left square of a $4\times4$ square in $5\cdot5=25$ ways, so there are 25 $4\times4$ squares. Similarly, there are 16 $5\times5$ squares, 9 $6\times6$ squares, 4 $7\times7$ squares and 1 $8\times8$ square. There are a total of $18+25+16+9+4+1=\boxed{73}$ squares containing at least 5 black squares.